p-Toluenesulfonic acid → Ethyl (2-bromo-4,5-difluorobenzoyl)acetate

HRID 2232079Notes

Reaction equation

HRID 2232079 reaction equation
[Br:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Br:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14347789Diethyl (2-bromo-4,5-difluorobenzoyl)malonate

Product 1

HCID 13912599Ethyl (2-bromo-4,5-difluorobenzoyl)acetateYield 84.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of diethyl (2-bromo-4,5-difluorobenzoyl)malonate (75.6 g) in water (100 ml) is added p-toluenesulfonic acid (0.3 g), and the mixture is refluxed for 3 hours. After cooling, the reaction mixture is extracted with dichloromethane. The dichloromethane layer is washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue is distilled to give ethyl (2-bromo-4,5-difluorobenzoyl)acetate (52.0 g), b.p. 105°-115° C. (0.15 mmHg).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted with dichloromethane
  4. washThe dichloromethane layer is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-82cc8cba5b594f5c9d9e360d2b1958ea
Source dataset
uspto-grants-1988_11
Patent number
US04786649

Reaction notes

Loading…